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Identification and Determination of Ketotifen Hydrogen Fumarate, Azelastine Hydrochloride, Dimetindene Maleate and Promethazine Hydrochloride by Densitometric Method

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Identification and Determination of Ketotifen Hydrogen Fumarate, Azelastine Hydrochloride, Dimetindene Maleate and Promethazine Hydrochloride by Densitometric Method Acta Poloniae Pharmaceutica ñ Drug Research, Vol. 70 No. 6 pp. 951ñ959, 2013 ISSN 0001-6837 Polish Pharmaceutical Society ANALYSIS IDENTIFICATION AND DETERMINATION OF KETOTIFEN HYDROGEN FUMARATE, AZELASTINE HYDROCHLORIDE, DIMETINDENE MALEATE AND PROMETHAZINE HYDROCHLORIDE BY DENSITOMETRIC METHOD ELØBIETA WYSZOMIRSKA1*, KRYSTYNA CZERWI—SKA1, ELØBIETA KUBLIN1 and ALEKSANDER P. MAZUREK1,2 1Department of Basic and Applied Pharmacy, National Medicines Institute, 30/34 Che≥mska St. 00-725 Warszawa, Poland 2Department of Drug Chemistry, Medical University of Warsaw, 1 Banacha St., 02-097 Warszawa, Poland Abstract: Conditions for determination of: ketotifen hydrogen fumarate, azelastine hydrochloride, dimetindene maleate and promethazine hydrochloride by densitometric method in substances and pharmaceuticals were pro- vided. Maximum wavelenghts were: 228 nm for ketotifen hydrogen fumarate, 295 nm for azelastine hydrochlo- ride, 265 nm for dimetindene maleate and 255 nm for promethazine hydrochloride. The limits of quantification were in the ranges of 0.2ñ5 µg/spot. The statistical data showed adequate accuracy and precision of developed methods. Keywords: ketotifen hydrogen fumarate, azelastine hydrochloride, dimetindene maleate, promethazine hydrochloride, histamine antagonist, densitometry Allergy means all excessive reactions of healthy people to neutral substances. Histamine is a physiologically active, endoge- nous substance that activates H1 and H2 receptors. It is responsible for allergic reaction in our body. The mechanism of action of antihistamines is based on their competitive and reversible connection between H1 and H2 receptors. It annihilates effects of C23H23NO5 S M.w. 425.5 histamine as a mediator of inflammation and Ketotifen hydrogen fumarate - 4-(1-Methylpiperidin-4-ylidene)- immune response (1, 2). 4,9-dihydro-10H-benzo[4,5]cyclohepta[1,2-b]thiophen-10-one Ketotifen hydrogen fumarate, azelastine hydrogen (E)-butenedioate hydrochloride, dimetindene maleate and promet- hazine hydrochloride are histamine antagonists Azelastine (as hydrochloride) is a II genera- medicines usually used in allergy treatment. tion antihistamine drug. Not only does it block Therefore, these medicines were chosen for this receptors for H1, but also inhibits the release of his- study. tamine. Following oral administration, it is metab- Ketotifen (as hydrogen fumarate) is able to olized and a major metabolite, which is N- inhibit the release of histamine, other relay demethylazelastine, shows properties of antihista- basophils and mast cells. It causes long-lasting inhi- mines. It is used in symptomatic treatment of aller- bition of histamine reactions. It is effective in the gies and as an adjunct in treatment of bronchial treatment of allergic diseases as well as asthma. It is asthma (1). used to prevent asthma attacks caused by allergy, it also works antianafilactically (1, 2). * Corresponding author: e-mail: [email protected] 951 952 ELØBIETA WYSZOMIRSKA et al. chemiluminescence method (3) and in plasma using HPLC method with a mass spectrometry detector (4). Azelastine, its enantiomers and metabolites were determined in rats plasma using coupling HPLC method with a β-cyclodextrin chiral sta- tionary phase to ion-spray tandem mass spectrom- etry. Additionally, an enatioselective assay was compared to another assay using electrokinetic capillary chromatography with β-cyclodextrin C H Cl N O M.w. 418.4 22 25 2 3 β Azelastine hydrochloride - 4-(4-Chlorobenzyl)-2-[(4RS)-1- and carboxymethyl- -cyclodextrin in polyacryl- methylhexahydro-1H-azepin-4-yl]phthalazin-1(2H)-one amide-coated capillaries (5). Moreover, HPLC hydrochloride method, with a mass spectrometry detector and chiral column, was used to determine azelastine in Dimetindene (as maleate) is a I generation plasma (6). antihistamine. It shows a very strong antipruritic Liquid chromatography (LC) with ZIC-HILIC activity. It is administered orally: retard tablet column and UV detector was used to determine (every 12 h) or drops and topically on the skin as a dimetindene maleate in gel (7). Capillary elec- gel (1, 2). trophoresies (CE) with a diode array detection (DAD) was used to determine dimetindene binding to human plasma proteins (8). Promethazine hydrochloride was determined in medicinal products (9ñ14) using spectrophotometric method (9, 10), capillary electrophoresis (11), den- sitometry (12), portable system of programmable syringe pump with potentiometer (13) and highly accurate nephelometric titration (14). Voltammetric method with carbon paste electrode (15) and HPLC- ESI-MS (16) were used to determine promethazine C H N O M. w. 408.5 24 28 2 4 in biological material. Dimethindene maleate - N,N-Dimethyl-2-[3-[(RS)-1-(pyridin-2- yl)ethyl]-1H-inden-2-yl]ethanamine (Z)-butenedioate Due to a high incidence rate of allergic reac- tions, histamine antagonists are a widely used group of compounds. Cost effective and easy methods for Promethazine (as hydrochloride) is a phenothi- the determination are required as an alternative to azine derivative of commonly used, slow, but long- liquid chromatography. acting antihistaminic. It also has hypnotic proper- The purpose of the study was to develop a sen- ties, antiemetic, anticholinergic and analgesic. sitive, simple, and cost-effective TLC method for Promethazine as therapeutic doesnít affect cardio- identification and determination of discussed com- vascular system, neither does it work as psychotic or pounds: ketotifen hydrogen fumarate, azelastine neuroleptic (1, 2). hydrochloride, dimetindene maleate and promet- hazine hydrochloride. EXPERIMENTAL Reference materials Ketotifen hydrogen fumarate (Novartis), Azelastine hydrochloride (Ph. Eur.), Dimetindene C17H21ClN2S M.w. 320.9 maleate (Ph. Eur.), Promethazine hydrochloride (Ph. Promethazine hydrochloride - (2RS)-N,N-Dimethyl-1-(10H-phe- nothiazin-10-yl)propan-2-amine hydrochloride Eur.). Active substances From the literature on the subject it can be Ketotifen hydrogen fumarate (Novartis), concluded that during last years, ketotifen hydro- Azelastine hydrochloride (Meda Pharma), Dimetin- gen fumarate was determined in tablets using dene maleate (Novartis). Identification and determination of ketotifen hydrogen fumarate... 953 Medicinal products The following seven chromatographic systems were Ketotifen 1 mg tablets (Polfa Warszawa), used: Allergodil 0.1% solution (Meda Pharma), Fenistil 1 1. Merck HPTLC Silica gel 60 F254 chromato- mg/g gel (Novartis), Diphergan 25 mg dragÈes graphic plates and mobile phase: trichloromethane - (Jelfa). methanol - ammonia 25% (90 : 10 : 1, v/v/v) with chamber saturation; Reagents and apparatus 2. Merck HPTLC Silica gel 60 F254 chromato- Analytically pure and high purity reagents for graphic plates and mobile phase: diethylether ñ HPLC from Lab Scan, Merck HPTLC Silica gel 60 diethylamine (40 : 1, v/v); F254 and Merck HPTLC LiChrospher Silica gel 60 3. Merck HPTLC Silica gel 60 F254 chromato- RP-18 WF254s chromatographic glass plates, Hanau graphic plates and mobile phase: methanol - ammo- UV lamp, Camag automatic applicator, Shimadzu nia 25% (100 :1.5, v/v); CS 9000 densitometer, Dionex Ultimate 3000 liquid 4. Merck HPTLC LiChrospher Silica gel 60 chromatograph or Shimadzu liquid chromatograph RP-18 WF254s chromatographic plates and mobile with SPD-10 AVVP spectrophotometric detector, phase: acetonitrile ñ methanol - acetate buffer pH SCL-10 AVP autosampler and LC-10 AT VP pump. 5.5 (3 : 2 : 5 v/v/v); 5. Merck HPTLC Silica gel 60 F254 chromato- Qualitative analysis graphic plates and mobile phase: toluene - ethyl Standard solutions of ketotifen hydrogen acetate ñ acetic acid 100% (16 : 4 : 1, v/v/v); fumarate, azelastine hydrochloride, dimetindene 6. Merck HPTLC Silica gel 60 F254 chromato- maleate and promethazine hydrochloride in graphic plates and mobile phase: n-hexane ñ acetone methanol of the following concentrations: 1 mg/mL, ñ ammonia 25% (85 : 14 : 1, v/v/v); 0.1 mg/mL, 0.01 mg/mL were prepared. 7. Merck HPTLC Silica gel 60 F254 chromato- Quantities of 30, 20, 10, 5, 2.5, 2, 1.5, 1, 0.5, graphic plates and mobile phase: acetonitrile ñ water 0.25, 0.2, 0.1, 0.05 and 0.025 µg of active substances ñ ammonia 25% (90 : 10 : 1, v/v/v). were put as spots onto Merck HPTLC Silica gel 60 The plates were air dried and the spots posi- F254 or Merck HPTLC LiChrospher Silica gel 60 RP- tions were determined under 254 nm UV light and in 18 WF254s chromatographic plates (2 cm from the iodine vapors. Rf values were determined. Limits of edge and 2 cm from the bottom) and developed in detection (LOD) were established for all analyzed selected mobile phases up to 1 cm from the top edge. compounds by visual methods. Figure 1. UV spectrum of ketotifen hydrogen fumarate measured directly from the TLC plate 954 Table 1. Rf values and limits of detection for the tested compounds (gray fields refer to the mobile phase selected for the quantitative determination of a given compound). System 1 System 2 System 3 System 4 System 5 System 6 System 7 Limit of Limit of Limit of Limit of Limit of Limit of Limit of Tested compound Rf detection Rf detection Rf detection Rf detection Rf detection Rf detection Rf detection [µg/spot] [µg/spot] [µg/spot] [µg/spot] [µg/spot] [µg/spot] [µg/spot] ELØBIETA WYSZOMIRSKAetal. UV iodine UV iodine UV iodine UV iodine UV iodine UV iodine UV iodine [µg] [µg] [µg] [µg] [µg] [µg] [µg] [µg] [µg] [µg] [µg] [µg] [µg] [µg] Ketotifen hydrogen 0.96 0.25 0.1 0.34 0.25 - 0.58 0.25 0.25 0.15 0.1 0.25 0.02 0.25 0.25 0 0.25 0.25 0.5 0.25 0.25 fumarate Azelastine 0.54 0.2 0.1 0.28 0.1 0.5 0.49 0.1 0.05 0.5 0.1 0.1 0 0.1 0.1 0 0.25 0.25 0.36 0.1 0.1 hydrochloride Dimetindene 0.64 0.05 0.1 0.28 0.02 0.1 0.51 0.1 0.1 0.26 0.1 0.2 0 0.1 0.2 0 0.1 0.2 0.26 0.1 0.2 maleate Promethazine 0.96 0.1 0.1 0.44 0.05 - 0.62 0.1 0.25 0.09 0.1 0.25 0.06 0.1 0.25 0.16 0.1 0.25 0.6 0.15 0.25 hydrochloride Chromatographic systems: 1.
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